CN1869012A - Preparation method of 2-(4'-methyl benzene sulfonyl) ethyl propionate - Google Patents
Preparation method of 2-(4'-methyl benzene sulfonyl) ethyl propionate Download PDFInfo
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- CN1869012A CN1869012A CN 200610085993 CN200610085993A CN1869012A CN 1869012 A CN1869012 A CN 1869012A CN 200610085993 CN200610085993 CN 200610085993 CN 200610085993 A CN200610085993 A CN 200610085993A CN 1869012 A CN1869012 A CN 1869012A
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- toluene
- ethyl propionate
- preparation
- base
- reaction
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Abstract
A process for preparing 2-(4'methylbenzosulfonyl) ethyl propionate includes such steps as adding toluene, P-toluene sulfuryl chloride and sodium hydroxide or potassium carbonate or CaO into reactor, dripping ethyl L-lactate at a temp lower than 10 deg.C, reaction, adding water, stirring, regulating pH=6-7, removing lower-layer water, and negative-pressure distilling to remove toluene and obtain product.
Description
Technical field:
The present invention relates to a kind of production technique of herbicide intermediate, be specifically related to the preparation method of a kind of 2-(4 '-toluene sulfonic acide base) ethyl propionate.
Background technology:
2-(4 '-toluene sulfonic acide base) ethyl propionate is the important intermediate of phenoxy carboxylic acid herbicidess such as synthetic quizalofopPethyl and fenoxapropPethyl, and this compound has unique optics and biological activity, has vast market prospect.Its molecular formula: C
12H
16O
5S
Structural formula:
Current, to synthesizing of 2-(4 '-toluene sulfonic acide base) ethyl propionate, be to adopt traditional triethylamine technology basically, not only there is the defective that speed of response is slow, transformation efficiency is low in it, but also exists the triethylamine rate of recovery low, the shortcoming that environmental pollution is big.
Summary of the invention:
Technical problem to be solved by this invention is: provide a kind of improved, can improve transformation efficiency and speed of response, and the preparation method of less 2-(the 4 '-toluene sulfonic acide base) ethyl propionate of environmental pollution.Its technical scheme is: the preparation method of a kind of 2-(4 '-toluene sulfonic acide base) ethyl propionate, it is characterized in that: will be through the Tosyl chloride of metering, toluene and acid binding agent drop in the reactor, under not being higher than 10 ℃ condition with L-ethyl lactate agitation and dropping in reaction system, dropwise follow-up continuation of insurance temperature reaction 2-5 hour, residual until the Tosyl chloride reaction is zero substantially, after reaction finishes, the water that in system, adds metering, cross after the stirring and dissolving to still kettle, keep at normal temperatures the pH value of system being adjusted to 6-7 with technical hydrochloric acid, under the negative pressure toluene distillation in the system is come out behind the branch sub-cloud water, promptly get 2-(4 '-toluene sulfonic acide base) ethyl propionate.
The mol ratio of above-mentioned Tosyl chloride, toluene, acid binding agent and L-ethyl lactate is 1: 6.5-8: 1.5-2.5: 1.05-1.4.
Above-mentioned acid binding agent is sodium hydroxide or salt of wormwood or calcium oxide.
Its technique effect is: the acid binding agent among the present invention is owing to adopt sodium hydroxide or salt of wormwood or calcium oxide, and with the traditional triethylamine of its replacement, so both improved speed of response significantly, to need nearly 40 hours reaction times to shorten to 2-5 hour originally, its yield is also significantly risen, can be up to more than 97%, the highest yield can reach 99%; Simultaneously, owing to adopt lower sodium hydroxide of cost value or salt of wormwood or calcium oxide to replace expensive triethylamine, so greatly reduce production cost; In addition, preparation method's technology of the present invention is fairly simple, has also alleviated pollution and labor capacity.
Embodiment:
In enamel reaction still, drop into the toluene of 870kg grade oil and the sodium hydroxide (NaOH) or the salt of wormwood (K of 435kg technical grade
2CO
3) or calcium oxide (CaO), open water coolant and stir and drop into 250kg, content is 99.5% Tosyl chloride, 186kg in reactor, dripping suction header tank in advance below 10 ℃, content is 99.5% L-ethyl lactate, dropwise follow-up continuation of insurance temperature reaction 2-5 hour, residual until the Tosyl chloride reaction is zero substantially, after reaction finishes, the water that in system, adds 600kg, cross after the stirring and dissolving to still kettle, keep at normal temperatures the pH value of system being adjusted to 6-7 with technical hydrochloric acid, under the negative pressure toluene distillation is come out behind the branch sub-cloud water, resistates is a sulfonated bodies in the still, i.e. 2-(4 '-toluene sulfonic acide base) ethyl propionate.Content reaches 98%, yield 〉=97%.Its chemical equation is as follows:
Claims (3)
1, the preparation method of a kind of 2-(4 '-toluene sulfonic acide base) ethyl propionate, it is characterized in that: will be through the Tosyl chloride of metering, toluene and acid binding agent drop in the reactor, under not being higher than 10 ℃ condition with L-ethyl lactate agitation and dropping in reaction system, dropwise follow-up continuation of insurance temperature reaction 2-5 hour, residual until the Tosyl chloride reaction is zero substantially, after reaction finishes, the water that in system, adds metering, cross after the stirring and dissolving to still kettle, keep at normal temperatures the pH value of system being adjusted to 6-7 with technical hydrochloric acid, under the negative pressure toluene distillation in the system is come out behind the branch sub-cloud water, promptly get 2-(4 '-toluene sulfonic acide base) ethyl propionate.
2, the preparation method of a kind of 2-according to claim 1 (4 '-toluene sulfonic acide base) ethyl propionate, it is characterized in that: the mol ratio of described Tosyl chloride, toluene, acid binding agent and L-ethyl lactate is 1: 6.5-8: 1.5-2.5: 1.05-1.4.
3, the preparation method of a kind of 2-according to claim 1 (4 '-toluene sulfonic acide base) ethyl propionate, it is characterized in that: described acid binding agent is sodium hydroxide or salt of wormwood or calcium oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610085993 CN1869012A (en) | 2006-06-13 | 2006-06-13 | Preparation method of 2-(4'-methyl benzene sulfonyl) ethyl propionate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610085993 CN1869012A (en) | 2006-06-13 | 2006-06-13 | Preparation method of 2-(4'-methyl benzene sulfonyl) ethyl propionate |
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| Publication Number | Publication Date |
|---|---|
| CN1869012A true CN1869012A (en) | 2006-11-29 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| CN 200610085993 Pending CN1869012A (en) | 2006-06-13 | 2006-06-13 | Preparation method of 2-(4'-methyl benzene sulfonyl) ethyl propionate |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241611A (en) * | 2011-05-18 | 2011-11-16 | 江苏雪豹日化有限公司 | Preparation method of S(-) ethyl p-methyl benzenesulfonyl propionate |
| CN102584724A (en) * | 2012-02-06 | 2012-07-18 | 京博农化科技股份有限公司 | Preparation method for quizalofop-p-ethyl |
| CN103755602A (en) * | 2013-12-24 | 2014-04-30 | 江苏天容集团股份有限公司 | Synthetic method of L-p-toluenesulfonyl ethyl lactate |
| CN108276313A (en) * | 2018-02-27 | 2018-07-13 | 东南大学 | A method of synthesizing (S) -2- p-toluenesulfonyl ethyl propionates using micro flow field technology continuous flow |
| CN109836456A (en) * | 2017-11-28 | 2019-06-04 | 利尔化学股份有限公司 | A kind of preparation method of diethyl methyl-phosphonite |
-
2006
- 2006-06-13 CN CN 200610085993 patent/CN1869012A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241611A (en) * | 2011-05-18 | 2011-11-16 | 江苏雪豹日化有限公司 | Preparation method of S(-) ethyl p-methyl benzenesulfonyl propionate |
| CN102241611B (en) * | 2011-05-18 | 2014-02-26 | 江阴市雪豹精细化工研究所 | Preparation method of S(-) ethyl p-methyl benzenesulfonyl propionate |
| CN102584724A (en) * | 2012-02-06 | 2012-07-18 | 京博农化科技股份有限公司 | Preparation method for quizalofop-p-ethyl |
| CN102584724B (en) * | 2012-02-06 | 2016-06-15 | 京博农化科技股份有限公司 | A kind of preparation method of Quizalotop-ethyl |
| CN103755602A (en) * | 2013-12-24 | 2014-04-30 | 江苏天容集团股份有限公司 | Synthetic method of L-p-toluenesulfonyl ethyl lactate |
| CN103755602B (en) * | 2013-12-24 | 2016-01-20 | 江苏天容集团股份有限公司 | The synthetic method of L-ethyl p-luenesulfonyl lactate |
| CN109836456A (en) * | 2017-11-28 | 2019-06-04 | 利尔化学股份有限公司 | A kind of preparation method of diethyl methyl-phosphonite |
| CN109836456B (en) * | 2017-11-28 | 2021-06-29 | 利尔化学股份有限公司 | Preparation method of diethyl methylphosphonite |
| CN108276313A (en) * | 2018-02-27 | 2018-07-13 | 东南大学 | A method of synthesizing (S) -2- p-toluenesulfonyl ethyl propionates using micro flow field technology continuous flow |
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